Potassium Carbonate → HCID 86761923, compound

HRID 448568

Reaction equation

[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][CH3:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:17]1[N:22]=[CH:21][N:20]=[C:19]([N:23]2[C:31]3[C:26](=[CH:27][C:28]([S:32]([CH3:35])(=[O:34])=[O:33])=[CH:29][CH:30]=3)[CH2:25][CH2:24]2)[CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>CC(N(C)C)=O.C(Cl)Cl.[Cl-].[Na+].O>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([C:17]2[CH:18]=[C:19]([N:23]3[C:31]4[C:26](=[CH:27][C:28]([S:32]([CH3:35])(=[O:33])=[O:34])=[CH:29][CH:30]=4)[CH2:25][CH2:24]3)[N:20]=[CH:21][N:22]=2)[CH3:15])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 7b (0.14 g, 2.1 eq), 6a (0.1 g, 0.3 mmol) and potassium carbonate (0.1 g, 2.2 eq) in 1 mL of DMA was heated up to 90° C. for 48 h then cooled down to room temperature and diluted with DCM (2 mL) and brine (2 mL). The layers were separated and the aqueous extracted with DCM (2×2 mL). The combined extracts were washed with brine (2×50 mL), dried over magnesium sulfate, filtered and evaporated. The residue was diluted with acetonitrile and purified on preparative HPLC to afford 7c.

Workup

temperaturethen cooled down to room temperature
customThe layers were separated
extractionthe aqueous extracted with DCM (2×2 mL)
washThe combined extracts were washed with brine (2×50 mL)
dry with materialdried over magnesium sulfate
filtrationfiltered
customevaporated
additionThe residue was diluted with acetonitrile
custompurified on preparative HPLC

Sources & evidence

ORD record: ord-94807e5ba900447ca162d4865b48c8e6
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481731B2

Linked notes

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